N,N'-Dimethylethylenediamine → methyl (R)-2-methoxy-4-(4-methyl-2-oxooxazolidin-3-yl)benzoate

HRID 1803977

반응식

HRID 1803977 반응식
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[CH3:14][C@@H:15]1[CH2:19][O:18][C:17](=[O:20])[NH:16]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>[Cu]I.O.C1(C)C=CC=CC=1>[CH3:13][O:12][C:4]1[CH:3]=[C:2]([N:16]2[C@H:15]([CH3:14])[CH2:19][O:18][C:17]2=[O:20])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

참가 물질

8

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 2734858(R)-4-Methyloxazolidin-2-oneHCID 15128242Methyl 4-bromo-2-methoxybenzoate

생성물 1

HCID 67380952methyl (R)-2-methoxy-4-(4-methyl-2-oxooxazolidin-3-yl)benzoate

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

To a mixture of methyl 4-bromo-2-methoxybenzoate (5.8 mL), (R)-4-methyloxazolidin-2-one (2 g) described in Preparation Example 25, potassium carbonate (2.8 g) and copper (I) iodide (760 mg) were added toluene (10 mL) and N,N′-dimethylethylenediamine (880 μL), and the mixture was refluxed for 8 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (hexane:ethyl acetate) to give methyl (R)-2-methoxy-4-(4-methyl-2-oxooxazolidin-3-yl)benzoate (2.1 g). Methyl (R)-2-methoxy-4-(4-methyl-2-oxooxazolidin-3-yl)benzoate (2.1 g) was dissolved in methanol (8 mL) and tetrahydrofuran (8 mL), 1N aqueous sodium hydroxide solution (16 mL) was added, and the mixture was stirred at room temperature for 3 hr. 1N hydrochloric acid (16 mL) was added, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The title compound (2.2 g) was obtained.

후처리

  1. temperaturethe mixture was refluxed for 8 hr
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography (hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-d41c5d71014b4838a42e2ed6dfd84f18
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354401B2

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